Winter Walk on Wilson

Winter Walk on Wilson
Friday, December 5th
5:00pm – 8:30pm
FREE EVENT! RSVP to win prizes!

The Uptown Chamber of Commerce is hosting our 11th Annual WINTER WALK ON WILSON on Friday, December 5th, 2025 from 5:00 – 8:30 PM. This FREE event features sweet treats, warm drinks, and menu samples offered by local Uptown businesses and organizations, live holiday music along the Wilson and Broadway commercial corridors, a pop-up holiday market, and photo ops with Uptown’s own Panda Claus!

PRIZE ALERT #1: The Uptown Chamber will be awarding prizes to a select few who RSVP for this free event! Click here.

PRIZE ALERT #2: Help us light the night by wearing anything that lights up for your chance to be spotted and awarded a surprise gift from the Uptown Chamber of Commerce including gift cards to local businesses and swag!

5:00-8:30PM
Small Business Activations!
Stroll along Wilson Avenue to experience the holiday cheer of live performances and tasty offerings by Uptown's small businesses!

Participating Uptown small businesses/orgs:
Stay tuned for a digital map and guide!

2Bears Tavern Uptown
Broadway Bikes
Chicago Fair Trade Museum + Store
Chicago Market
Crema Shop
Downstate Donuts
Everybody's Coffee
Fauna Veterinary Care
Joel Hall Dancers & Center
Las Piñatas
Marina's Bistro @ Alexis Zimmer State Farm
Missio Dei Uptown
My Art House Studio
Nabala Cafe
Poor Boy Rich Taste
Sky's Beverage Depot
StudioUs
Sunflour Bakery @ JT Training Studios
TERRACE
Trading Post Pet Supplies
Uplift Community High School
Uptown Baptist Church
Uptown Church
Uptown Taproom
Wagnolia
Yoga Body Elements

5:00 - 8:30PM
Music and Caroling!
Catch these roaming performers along Wilson Avenue on the night of the event:

Beaux & Belles
Faces for Radio
Lakeside Pride Instrumental Carolers
The Pippins
More TBA

5:00-8:30PM
Uptown Holiday Market!
Chicago Market, 4618 N. Broadway
Step inside the Uptown Holiday Market featuring retail vendors and photo ops with Uptown's own Panda Claus!
Click here for vendor application.